EP0880506A1

EP0880506A1 - Process for the preparation of substituted cyanophenyl uracils from substituted aminoalkene acid cyanophenyl amides

Info

Publication number: EP0880506A1
Application number: EP97902232A
Authority: EP
Inventors: Roland Andree; Mark Wilhelm Drewes; Reinhard Lantzsch; Heinz-Jürgen Wroblowsky
Original assignee: Bayer AG
Current assignee: Bayer CropScience AG
Priority date: 1996-02-08
Filing date: 1997-01-27
Publication date: 1998-12-02
Also published as: US6169182B1; JP2000504675A; WO1997029094A1; US6262291B1; AU1595397A; MX9806195A; TW394762B; DE19604582A1

Abstract

The invention relates to a new process for the preparation of substituted cyanophenyl uracils of the general formula (I), in which R<1>, R<2>, R<3> and R<4> have the meanings given in the description, said compounds being known as herbicidal compounds. The invention also relates to new substituted aminoalkene acid cyanophenyl amides as intermediates therefore and an inventive process for the preparation thereof.

Description

METHOD FOR PRODUCING SUBSTITUTED CYANOPHANYLURACILE FROM SUBSTITUTED AMINOALKENIC ACID-CYANOPHENYLAMIDES

The invention relates to a new process for the preparation of substituted cyanophenyluracils, which are known as herbicidally active compounds, new substituted aminoalkenoic acid cyanophenyl amides as intermediates therefor and an inventive process for their preparation.

It is known that certain substituted cyanophenyluracils by reacting corresponding aminoalkenoic esters with corresponding cyanophenyl isocyanates or with cyanophenyl urethanes in the presence of reaction auxiliaries, such as e.g. Sodium hydride can be produced (see. EP 648749). With this procedure, however, the yield and the quality of the products obtained in this way are not always entirely satisfactory, and the reaction components required are unsuitable for technical matters.

It is also known that certain substituted phenyluracils can be prepared by reacting corresponding substituted aminoalkenoic acid phenylamides with suitable carbonic acid derivatives (cf. WO 95/32952). However, the synthetic route described in this publication is multi-stage and complex.

The present invention relates to

(a) a process for the preparation of substituted cyanophenyluracils of the general formula (I)

in which

R ^{1 represents} optionally substituted alkyl, R ^{2 represents} hydrogen, halogen or alkyl,

R ^{3 represents} hydrogen or halogen and

R ^{4 represents} amino, halogen or the grouping -N (R ⁵ ) SO ₂ R ⁶ ,

wherein

R ^{5 represents} hydrogen or alkyl which is optionally substituted,

Alkylcarbonyl, alkylsulfonyl, cycloalkylcarbonyl, cycloalkylsulfonyl, arylcarbonyl or arylsulfonyl and

R ⁶ represents optionally substituted alkyl, cycloalkyl or aryl,

characterized in that substituted aminoalkenoic acid-cyanophenyl amides of the general formula (II)

in which

R ¹ , R ² , R ³ and R ^{4 have} the meanings given above,

with carbonic acid derivatives of the general formula (III)

Z'-CO-Z ² (III),

in which

Z ¹ and Z ^{2 are} identical or different and represent halogen, alkoxy, aryloxy, imidazolyl or triazolyl, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, at temperatures between -20 ° C. and + 150 ° C.,

(b) new substituted aminoalkenoic acid-cyanophenylamides of the general formula (II)

in which

R ^{1 represents} optionally substituted alkyl,

R _► 2 represents hydrogen, halogen or alkyl,

R represents hydrogen or halogen and

R ^{4 represents} amino, halogen or the grouping -N (R) SO ₂ R,

woπn

R stands for hydrogen or for optionally substituted alkyl, alkylcarbonyl, alkylsulfonyl, cycloalkylcarbonyl, cycloalkylsulfonyl, arylcarbonyl or arylsulfonyl and

R represents in each case optionally substituted alkyl, cycloalkyl or aryl, and

(c) a process for the preparation of substituted aminoalkenoic acid-cyano-phenylamides of the general formula (II), characterized in that cyanophenylpyrimidinones of the general formula (IV) in which

R 1, R, R and R have the meanings given above,

with basic compounds in the presence of a diluent at temperatures between -20 ° C and + 100 ° C.

The invention also relates to the new route for the preparation of substituted cyanophenyluracils of the general formula (I), in which the steps generally set out above under (c) and (a) are carried out.

It can be described as surprising that this new route enables the substituted cyanophenyluracils of the general formula (I) to be considerably simpler

Way as well as in higher yields and improved quality can be produced. In particular, the smooth ring-opening reaction of the cyanophenylpyrimidones of the formula (IV) to the substituted aminoalkenoic acid-cyanophenylamides of the formula (II) represents a very surprising new possibility for the preparation of substituted β-aminoalkenoic acid arylamides.

The invention preferably relates to the preparation of compounds of the formula (I) and new compounds of the formula (II), in each of which

R ^{1 represents} optionally substituted by fluorine and or chlorine alkyl having ¹ to 4 carbon atoms,

R ^{2 represents} hydrogen, fluorine, chlorine, bromine or alkyl having 1 to 4 carbon atoms,

R represents hydrogen, fluorine, chlorine or bromine and R ^{4 represents} amino, fluorine, chlorine or the grouping -N (R ⁵ ) SO ₂ R ⁶ , in which

R ⁵ for hydrogen or for alkyl, alkylcarbonyl or alkylsulfonyl, each optionally substituted by fluorine and / or chlorine, each having 1 to 6 carbon atoms in the alkyl groups, for cycloalkylcarbonyl or cycloalkylsulfonyl, each optionally substituted by fluorine and / or chlorine, each having 3 to 6 Carbon atoms in the cycloalkyl groups, or phenylcarbonyl or phenylsulfonyl optionally substituted by fluorine and / or chlorine, and

R ^{6 represents} alkyl with 1 to 6 carbon atoms optionally substituted by fluorine and / or chlorine, cycloalkyl with 3 to 6 carbon atoms optionally substituted by fluorine and / or chlorine, or phenyl optionally substituted by fluorine and / or chlorine

The invention relates in particular to the preparation of compounds of the formula (I) and new compounds of the formula (II), in each of which

R ¹ each represents methyl or ethyl optionally substituted by fluorine and or chlorine,

R ^{2 represents} hydrogen, fluorine, chlorine, bromine, methyl or ethyl,

R represents hydrogen, fluorine or chlorine and

R ^{4 represents} fluorine, chlorine or the grouping -N (R ⁵ ) SO ₂ R ⁶ , in which

R represents hydrogen or methyl, ethyl, n- or i-propyl, acetyl, propionyl, methylsulfonyl or ethyl sulfonyl, optionally substituted by fluorine and / or chlorine, for cyclopropylcarbonyl, cyclobutyl optionally substituted by fluorine and / or chlorine carbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl or cyclohexylsulfonyl, or phenylcarbonyl or phenylsulfonyl optionally substituted by fluorine and / or chlorine, and R ⁶ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, optionally substituted by fluorine and / or chlorine, for each optionally substituted by fluorine and / or chlorine Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or for phenyl optionally substituted by fluorine and / or chlorine.

If, for example, 3- (4-cyano-2,5-difluorophenyl) -6-trifluoromethyl-pyrimidin-4-one is used as starting material in process step (process (c)) described above (process (c)) and the resulting product is used Product according to the process step (process (a)) described above under (a), for example with phosgene, the overall course of the reaction can be outlined using the following formula:

Formula (III) provides a general definition of the carbonic acid derivatives to be used as starting materials in process (a) according to the invention for the preparation of compounds of formula (I). In formula (III), Z ¹ and Z ^{2 are the} same or different and are preferably fluorine, chlorine, bromine, C ₁ -C ₄ alkoxy, phenoxy, imidazolyl or triazolyl, in particular chlorine, methoxy, ethoxy or phenoxy.

Examples of the starting materials of the formula (III) are:

Phosgene (as well as its "dimers" or "trimers" - diphosgene or triphosgene),

Dimethyl carbonate, diethyl carbonate, diphenyl carbonate, chloroformate methyl ester and ethyl ester and carbonyl bis-imidazole. The starting materials of the formula (III) are known synthetic chemicals.

Formula (IV) provides a general definition of the cyanophenylpyrimidinones to be used as starting materials in process (c) according to the invention for the preparation of compounds of the formula (II). In the formula (IV), R ¹ , R ² , R ³ and R ⁴ preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R ¹ , R ² , R ³ and R ^{4 were} given.

The starting materials of the formula (IV) are known and / or can be prepared by known processes (cf. DE 4431218, production examples).

Process (c) according to the invention is carried out using a basic compound. All conventional inorganic or organic bases are suitable as such. These include, for example, alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as, for example, lithium, sodium, potassium or calcium hydride, sodium or potassium amide, sodium - or potassium methylate, sodium or potassium ethylate, sodium or potassium n- or i-propylate, sodium or potassium t-butoxide, lithium, sodium, potassium, magnesium or calcium hydroxide, Ammonium hydroxide, sodium or potassium acetate, ammonium acetate, sodium, potassium, magnesium or calcium carbonate, sodium or potassium hydrogen carbonate, ammonium carbonate and tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).

Alkali metal carbonates, e.g. Sodium or potassium carbonate, alkali metal hydroxides such as e.g. Sodium or potassium hydroxide, as well as alkali metal alcoholates, such as e.g. Sodium or potassium methylate, sodium or potassium ethylate, sodium or potassium t-butoxide are particularly preferably used as basic compounds in process (c) according to the invention.

Suitable diluents for carrying out process (c) according to the invention are water and organic solvents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated Hydrocarbons such as gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyelohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, n-, i-, s- or t-butanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether , their mixtures with water or pure water.

Water or alcohols, e.g. Methanol or ethanol are particularly preferably used as diluents in process (c) according to the invention.

The reaction temperatures can be carried out when carrying out the process according to the invention

Process (c) can be varied over a wide range. In general, temperatures between -20 ° C and + 100 ° C, preferably between -5 ° C and + 80 ° C, in particular between + 10 ° C and + 60 ° C.

Process (c) according to the invention is generally carried out under normal pressure. However, it is also possible to carry out process (c) according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.

To carry out process (c) according to the invention, generally 0.9 to 1.5 mol, preferably 0.95 to 1.2 mol, of a basic compound are used per mol of cyanophenylpyrimidone of the formula (IV).

The reaction components are generally mixed at room temperature - or, if appropriate, with gentle cooling - and the reaction mixture is stirred at the temperature required in each case until the end of the reaction.

The products can be worked up and isolated in the customary manner. For example, the organic is shaken with water and a practically immiscible organic solvent, such as methylene chloride, with water Phase separated and dried. The solvent is distilled off under reduced pressure and the residue is optionally purified by a customary method (for example chromatography, recrystallization). The crude product from process (c) can, however, optionally also be used for the reaction according to process (a) without further purification.

Process (a) according to the invention for the preparation of the compounds of the formula (I) is preferably carried out in the presence of a suitable reaction auxiliary. The usual inorganic or organic bases or acid acceptors are generally suitable as reaction auxiliaries. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, hydrogen bicarbonates, hydrides, hydroxides or alkanolates, such as, for example, sodium, potassium or calcium acetate, lithium, sodium , Potassium or calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium bicarbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or Calcium hydroxide, sodium or potassium methoxide, ethanolate, n- or i-propanolate, n-, i-, s- or t-butanolate; basic organic nitrogen compounds such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, N, N- Dimethylbenzylamine, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-dimethyl, 2,6-

Dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, 1,4-diazabicyclo [2,2, 2] octane (DAB-CO), 1,5-diazabicyclo [4,3,0] non-5-ene (DBN), or 1,8 diazabicyclo [5,4,0] -undec-7-ene (DBU).

Suitable diluents for carrying out process (a) according to the invention are preferably inert organic solvents. These include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyelohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers, such as diethyl ether, diisopropyl ether,

Dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles, such as acetonitrile, propionitrile or benzonitrile; Amides, such as N, N-dimethylformamide, NN-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamid; Esters such as methyl acetate or ethyl acetate, and sulfoxides such as dimethyl sulfoxide.

The reaction temperatures can be varied within a substantial range when carrying out process (a) according to the invention. In general, temperatures between -20 ° C and + 150 ° C, preferably between -10 ° C and + 120 ° C, in particular between 0 ° C and 100 ° C.

Process (a) according to the invention is generally carried out under normal pressure. However, it is also possible to carry out process (a) according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.

To carry out process (a) according to the invention, generally 1.0 to 5.0 mol, preferably 1.1 to 2.5 mol, of carbonic acid derivative of the formula (III) and. Are employed per mol of substituted aminocrotonic acid-cyanophenylamide of the formula (II) optionally 1.0 to 5.0 mol, preferably 1.2 to 2.5 mol, of reaction auxiliaries. The reaction is carried out, worked up and isolated according to known methods.

The cyanophenyluracils to be prepared according to the invention are already known as herbicidally active compounds (cf. EP 648749).

Preparation Examples:

example 1

(Method (c))

30.3 g (0.10 mol) of 3- (4-cyano-2,5-difluorophenyl) -6-trifluoromethyl-pyrimidin-4-one, 20 ml of 5N sodium hydroxide solution (0.10 mol of NaOH) and 300 ml of water are mixed at room temperature (approx. 20 ° C.) and the mixture is stirred at this temperature for approx. 20 hours. The crystalline reaction product is isolated by suction, washed with water and dried in a desiccator over phosphorus (V) oxide.

27.7 g (93.3%, ie 89% of theory) of N- (4-cyano-2,5-difluorophenyl) -3-amino-4,4,4-trifluoro-2-butenamide are obtained from the melting point 127 ° C.

Example 2

(Procedure (c)

0.8 g (2.7 mmol) of 3- (4-cyano-2,5-difluorophenyl) -6-trifluoromethyl-pyrimidin-4-one, 0.15 g (2.7 mmol) of sodium methylate and 10 ml Ethanol are mixed at room temperature (approx. 20 ° C) and the mixture is at this for approx. One hour Temperature stirred. The mixture is then concentrated in a water jet vacuum, the residue is shaken with water / methylene chloride, the organic phase is separated off, dried with sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate in a water jet vacuum.

0.6 g (76% of theory) of N- (4-cyano-2,5-difluorophenyl) -3-amino-4,4,4-trifluoro-2-butenamide of melting point 127 ° C. is obtained.

Example 3

(Method (a))

1.56 g (5 mmol) of N- (4-cyano-2,5-difluorophenyl) -3-amino-4,4,4-trifluoro-2-butenoic acid amide (93.3% strength) are in 20 ml of tetrahydrofuran dissolved and 0.3 g of an 80% suspension of sodium hydride in paraffin oil are added. The mixture is stirred at about 20 ° C. for about 30 minutes. Then 1.28 g (5.6 mmol) of diphenyl carbonate are added and the reaction mixture is heated under reflux for about 15 hours. After cooling, the mixture is concentrated in a water jet vacuum, the residue is taken up in water and the pH is adjusted to 3 by adding 2N hydrochloric acid. The product obtained in crystalline form is isolated by suction and dried over phosphorus (V) oxide under reduced pressure.

1.65 g (79.7%, ie 83% of theory) of 1- (4-cyano-2,5-difluorophenyl) -3,6-dihydro-2,6-dioxo-4-trifluoromethyl are obtained -l (2H) -pyrimidine with melting point 208 ° C. Example 4

(Method (a))

9.4 g (30 mmol) of N- (4-cyano-2,5-difluorophenyl) -3-amino-4,4,4-trifluoro-2-butenoic acid amide (93.3% strength) are dissolved in 200 ml of toluene dissolved and 6 ml of pyridine and 0.3 g of 4-dimethylamino-pyridine are added. At an internal temperature of about 40 ° C., about 5 g of phosgene are introduced and the reaction mixture is then stirred at about 40 ° C. for about 4 hours. After cooling, 200 ml of water are added, and after shaking well, the product which crystallizes is isolated by suction on clay.

3.7 g (39% of theory) of l- (4-cyano-2,5-difluorophenyl) -3,6-dihydro-2,6-dioxo-4-trifluoromethyl-l (2H) -pyrimidine are obtained melting point 208 ° C

Starting materials of the formula (TV):

Example (IV-n

A mixture of 3.0 g (18.3 mmol) of 6-trifluoromethyl-pyrimidin-4-one, 2.5 g (18.3 mmol) of potassium carbonate and 50 ml of dimethyl sulfoxide is stirred at 20 ° C. for 15 hours. Then 2.9 g (18.3 mmol) of 2,4,5-trifluoro-benzonitrile are added and the mixture is stirred at 60 ° C. for 8 hours. After concentration, the residue is stirred with water and the crystalline product is isolated by suction.

2.7 g (49% of theory) of 3- (4-cyano-2,5-difluorophenyl) -6-trifluoromethylpyrimidin-4-one with a melting point of 95 ° C. are obtained.

Claims

1. Process for the preparation of substituted cyanophenyluracils of the general formula (I)

in which

R ^{1 represents} optionally substituted alkyl,

R ^{2 represents} hydrogen, halogen or alkyl,

R ^{3 represents} hydrogen or halogen and

R ^{4 represents} amino, halogen or the grouping -N (R ⁵ ) SO ₂ R ⁶ ,

wherein

R ^{5 represents} hydrogen or represents optionally substituted alkyl, alkylcarbonyl, alkyl sulfonyl, cycloalkylcarbonyl, cycloalkylsulfonyl, arylcarbonyl or arylsulfonyl and

R ⁶ represents optionally substituted alkyl, cycloalkyl or aryl,

characterized in that substituted aminoalkenoic acid-cyano-phenylamides of the general formula (II) in which

R ¹ , R ² , R ³ and R ^{4 have} the meanings given above,

with carbonic acid derivatives of the general formula (III)

Z'-CO-Z ² (in),

in which

Z ¹ and Z ^{2 are} identical or different and represent halogen, alkoxy, aryloxy, imidazolyl or triazolyl,

if appropriate in the presence of a reaction auxiliary and, if appropriate, in the presence of a diluent at temperatures between -20 ° C. and + 150 ° C.

Process for the preparation of substituted aminoalkenourecyanophenylamides of the general formula (II)

in which R ¹ , R ² , R ³ and R ^{4 have} the meanings given in Claim 1, characterized in that cyanophenylpyrimidinones of the general formula (IV)

in which

R ¹ , R ² , R ³ and R ^{4 have} the meanings given in claim 1, with basic compounds in the presence of a diluent at temperatures between -20 ° C and + 100 ° C.

Process for the preparation of substituted cyanophenyluracils of the general formula (I) according to Claim 1, characterized in that starting from the cyanophenylpyrimidinones of the general formula (IV)

in which

R ¹ , R ² , R ³ and R ^{4 have} the meanings given in Claim 1 to aminoalkenoic acid cyanophenylamides of the general formula (II) in which

R ¹ , R ² , R ³ and R ^{4 have} the meanings given above, reacted and finally allowed to react further to the desired cyanophenyluracils according to the process of claim 1

Substituted aminoalkenoic acid-cyanophenylamides of the formula (II)

characterized in that

R ^{1 represents} optionally substituted alkyl,

R 2 represents hydrogen, halogen or alkyl,

R ^{3 represents} hydrogen or halogen and

R ^{4 represents} ammo, halogen or the grouping -N (R) SO ₂ R ⁶ ,

wonn

R stands for hydrogen or for optionally substituted alkyl, alkylcarbonyl, alkylsulfonyl, cycloalkylcarbonyl, cycloalkylsulfonyl, arylcarbonyl or arylsulfonyl and R ^{6 stands} for optionally substituted alkyl, cycloalkyl or aryl

Substituted aminoalkenoic acid-cyanophenylamides of the general formula

(II) according to claim 4, characterized in that

R ^{1 represents} alkyl with 1 to 4 carbon atoms optionally substituted by fluorine and or chlorine,

R ^{3 represents} hydrogen, fluorine, chlorine or bromine and

R ^{4 represents} amino, fluorine, chlorine or the grouping -N (R ⁵ ) SO ₂ R ⁶ , in which

R ^{5 represents} hydrogen or alkyl, alkylcarbonyl or alkylsulfonyl, each optionally substituted by fluorine and / or chlorine, each having 1 to 6 carbon atoms in the alkyl groups, each optionally substituted by fluorine and / or chlorine

Cycloalkylcarbonyl or cycloalkylsulfonyl each having 3 to 6 carbon atoms in the cycloalkyl groups, or for phenylcarbonyl or phenylsulfonyl optionally substituted by fluorine and / or chlorine, and

Process for the preparation of substituted cyanophenyluracils of the general formula (I) according to Claims 1 and 3, characterized in that R ^{1 represents} alkyl with 1 to 4 carbon atoms optionally substituted by fluorine and or chlorine,

R ^{3 represents} hydrogen, fluorine, chlorine or bromine and

R ⁵ for hydrogen or for alkyl, alkylcarbonyl or alkylsulfonyl, each optionally substituted by fluorine and / or chlorine, each having 1 to 6 carbon atoms in the alkyl groups, for cycloalkylcarbonyl or cycloalkylsulfonyl, each optionally substituted by fluorine and / or chlorine, each having 3 to 6 carbon atoms in the cycloalkyl groups, or represents phenylcarbonyl or phenylsulfonyl which may be substituted by fluorine and / or chlorine, and

R ^{6 represents} alkyl with 1 to 6 carbon atoms optionally substituted by fluorine and / or chlorine, cycloalkyl with 3 to 6 carbon atoms optionally substituted by fluorine and / or chlorine, or phenyl optionally substituted by fluorine and / or chlorine.

7. Substituted aminoalkenoic acid-cyanophenylamides of the general formula (II) according to claim 4, characterized in that

R ^{2 represents} hydrogen, fluorine, chlorine, bromine, methyl or ethyl,

R ^{"1 represents} hydrogen, fluorine or chlorine and

R ^{4 represents} fluorine, chlorine or the grouping -N (R ⁵ ) SO ₂ R ⁶ , in which R ^{5 represents} hydrogen or methyl, ethyl, n- or i-propyl, acetyl, propionyl, methylsulfonyl or ethylsulfonyl, each optionally substituted by fluorine and / or chlorine, for cyclopropylcarbonyl optionally substituted by fluorine and / or chlorine, Cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl or cyclohexylsulfonyl, or for phenylcarbonyl or phenylsulfonyl optionally substituted by fluorine and / or chlorine, and

R ⁶ for each optionally substituted by fluorine and / or chlorine

Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each optionally substituted by fluorine and / or chlorine, or for each optionally fluorine and / or chlorine-substituted phenyl.

8. A process for the preparation of substituted cyanophenyluracils of the general formula (I) according to Claims 1 and 3, characterized in that

R ^{2 represents} hydrogen, fluorine, chlorine, bromine, methyl or ethyl,

R ^{3 represents} hydrogen, fluorine or chlorine and

R ^{5 represents} hydrogen or methyl, ethyl, n- or i-propyl, acetyl, which is optionally substituted by fluorine and / or chlorine,

Propionyl, methylsulfonyl or ethylsulfonyl, for cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl or cyclohexylsulfonyl or cyclohexylsulfonyl or cyclohexylsulfonyl or cyclohexylsulfonyl, in each case optionally substituted by fluorine and / or chlorine phenylcarbonyl or phenylsulfonyl substituted by fluorine and / or chlorine, and

for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by fluorine and / or chlorine, for cyclo-propyl, cyclobutyl optionally substituted by fluorine and / or chlorine, Cyclopentyl or cyclohexyl, or phenyl optionally substituted by fluorine and / or chlorine.